N-Biphenyl thioureas as carboxylate receptors.: Effect of the ligand substituents on the geometry of the complexes

被引：24

作者：

Costero, Ana M. ^{[1
]}

Gavina, Pablo

Rodriguez-Muniz, Gemma M.

Gil, Salvador

机构：

[1] Univ Valencia, Dept Organ Chem, E-46100 Valencia, Spain

[2] Univ Valencia, Inst Ciencia Mol, Valencia, Spain

来源：

TETRAHEDRON | 2006年 / 62卷 / 36期

关键词：

D O I：

10.1016/j.tet.2006.06.058

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Six new biphenyl thiourea derivatives have been prepared to be used in carboxylate sensing. Experiments carried out with these ligands have demonstrated that the type of interaction with TBA carboxylates is strongly dependent on the substituents in the thiourea moiety. These interactions go from the formation of 1:1 hydrogen-bonded complexes to acid-base reactions. In addition, different geometries have been observed for the complexes being dependent on the conformations of the free ligands in solution. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：8571 / 8577

页数：7

共 33 条

[1] Dimeric self-assembling capsules derived from the highly flexible tribenzylamine skeleton [J].

Alajarín, M ;

Pastor, A ;

Orenes, RA ;

Steed, JW .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7091-7095

[2] Metal-enhanced H-bond donor tendencies of urea and thiourea toward anions:: Ditopic receptors for silver(I) salts [J].

Amendola, V ;

Esteban-Gómez, D ;

Fabbrizzi, L ;

Licchelli, M ;

Monzani, E ;

Sancenón, F .

INORGANIC CHEMISTRY, 2005, 44 (24) :8690-8698

[3] Anion-induced urea deprotonation [J].

Boiocchi, M ;

Del Boca, L ;

Esteban-Gómez, D ;

Fabbrizzi, L ;

Licchelli, M ;

Monzani, E .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (10) :3097-3104

[4] Nature of urea-fluoride interaction:: Incipient and definitive proton transfer [J].

Boiocchi, M ;

Del Boca, L ;

Gómez, DE ;

Fabbrizzi, L ;

Licchelli, M ;

Monzani, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (50) :16507-16514

[5] Fluorescent sensing of maleate versus fumarate by a neutral cyclohexane based thiourea receptor [J].

Costero, AM ;

Colera, M ;

Gaviña, P ;

Gil, S .

CHEMICAL COMMUNICATIONS, 2006, (07) :761-763

[6] Conformationally regulated fluorescent sensors.: Study of the selectivity in Zn2+ versus Cd2+ sensing [J].

Costero, AM ;

Gil, S ;

Sanchis, J ;

Peransí, S ;

Sanz, V ;

Williams, JAG .

TETRAHEDRON, 2004, 60 (30) :6327-6334

[7] Biphenyl macrolactams in anion complexation.: Selective naked-eye fluoride recognition [J].

Costero, AM ;

Bañuls, MJ ;

Aurell, MJ ;

Ward, MD ;

Argent, S .

TETRAHEDRON, 2004, 60 (42) :9471-9478

[8] A two-channel chemosensor for the optical detection of carboxylic acids, including cholic acid [J].

Esteban-Gómez, D ;

Fabbrizzi, L ;

Licchelli, M ;

Sacchi, D .

JOURNAL OF MATERIALS CHEMISTRY, 2005, 15 (27-28) :2670-2675

[9] Anion binding vs. deprotonation in colorimetric pyrrolylamidothiourea based anion sensors [J].

Evans, LS ;

Gale, PA ;

Light, ME ;

Quesada, R .

CHEMICAL COMMUNICATIONS, 2006, (09) :965-967

[10] MOLECULAR RECOGNITION - HYDROGEN-BONDING RECEPTORS THAT FUNCTION IN HIGHLY COMPETITIVE SOLVENTS [J].

FAN, E ;

VANARMAN, SA ;

KINCAID, S ;

HAMILTON, AD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (01) :369-370

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